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$137+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Calgary to Midway

Best flights from Calgary to Midway
Discover carefully curated flight deals from Calgary to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 28, 2025.

This Delta deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/96:30 amYYC - MDW
1 stop5h 39mDelta
Mon 1/121:49 pmMDW - YYC
1 stop8h 05mDelta
Deal found 12/26$226
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/169:45 pmYYC - MDW
2 stops23h 28mMultiple Airlines
Fri 1/235:01 pmMDW - YYC
1 stop27h 08mMultiple Airlines
Deal found 12/27$251
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:30 amYYC - MDW
1 stop5h 35mDelta
Mon 3/92:05 pmMDW - YYC
1 stop7h 40mDelta
Deal found 12/27$226
This Kiwi.com deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2412:30 amYYC - MDW
1 stop10h 15mMultiple Airlines
Sun 2/14:15 pmMDW - YYC
1 stop28h 20mMultiple Airlines
Deal found 12/28$262
This Delta deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/912:30 amYYC - MDW
1 stop10h 29mDelta
Tue 2/179:50 amMDW - YYC
2 stops10h 22mDelta
Deal found 12/26$253
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:30 amYYC - MDW
1 stop5h 35mDelta
Sun 3/159:35 amMDW - YYC
2 stops12h 23mDelta
Deal found 12/27$273
This Kiwi.com deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1912:30 amYYC - MDW
1 stop10h 35mMultiple Airlines
Sat 1/319:38 amMDW - YYC
2 stops32h 48mMultiple Airlines
Deal found 12/25$301
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/912:30 amYYC - MDW
1 stop17h 37mMultiple Airlines
Tue 2/1711:05 amMDW - YYC
1 stop10h 53mMultiple Airlines
Deal found 12/26$316
This Delta deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:30 pmYYC - MDW
2 stops17h 00mDelta
Thu 5/76:00 amMDW - YYC
2 stops18h 06mDelta
Deal found 12/25$322

Find flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Delta)

One-way from

$137
(Trip.com)

Popular in

July

Cheapest in

April

Average price

$296
Provider with most accurate pricing for Calgary-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago Midway flights.
Search Deals
From Calgary to Chicago Midway
Search Deals
One-way flight from Calgary to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 28, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 1/9

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Mon 1/12

1:49 pm-8:54 pm

1 stop8h 05m

$226

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 3/5

6:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Mon 3/9

2:05 pm-8:45 pm

1 stop7h 40m

$226

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 1/16

9:45 pm-10:13 pm

2 stops23h 28m

Chicago Midway

Fri 1/23

5:01 pm-7:09 pm

1 stop27h 08m

$251

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/9

12:30 am-11:59 am

1 stop10h 29m

Chicago Midway

Tue 2/17

9:50 am-7:12 pm

2 stops10h 22m

$253

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 1/24

12:30 am-11:45 am

1 stop10h 15m

Chicago Midway

Sun 2/1

4:15 pm-7:35 pm

1 stop28h 20m

$262

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 3/5

6:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Sun 3/15

9:35 am-8:58 pm

2 stops12h 23m

$273

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 1/19

12:30 am-12:05 pm

1 stop10h 35m

Chicago Midway

Sat 1/31

9:38 am-5:26 pm

2 stops32h 48m

$301

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 2/9

12:30 am-7:07 pm

1 stop17h 37m

Chicago Midway

Tue 2/17

11:05 am-8:58 pm

1 stop10h 53m

$316

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/4

6:30 pm-12:30 pm

2 stops17h 00m

Chicago Midway

Thu 5/7

6:00 am-11:06 pm

2 stops18h 06m

$322

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/15

6:30 am-5:34 pm

2 stops10h 04m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 20 results
1
2

Compare providers for flights from Calgary to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Calgary to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Calgary-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Calgary-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Calgary-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Calgary-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago Midway Airport?

    A quick flight from Calgary to Chicago Midway Airport can take about 5h 39m. Delta provides one of the quickest options available for as low as $226. Calgary and Chicago Midway Airport are separated by a distance of 1396 mi.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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